| 1. Round | 19/03/1999 | Tampa Bay Mutiny | - | D.C. United | 2:5 |  |
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| 2. Round | 02/04/1999 | MetroStars | - | D.C. United | 0:1 | ||||
| 2. Round | 09/04/1999 | New England Revolution | - | D.C. United | n.P. | ||||
| 2. Round | 16/04/1999 | D.C. United | - | San Jose Clash | n.P. | ||||
| 2. Round | 23/04/1999 | D.C. United | - | New England Revolution | 2:3 |  |
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| 3. Round | 07/05/1999 | D.C. United | - | MetroStars | 2:1 | ||||
| 3. Round | 14/05/1999 | Kansas City Wizards | - | D.C. United | n.P. | ||||
| 3. Round | 21/05/1999 | Miami Fusion | - | D.C. United | 1:3 | ||||
| 4. Round | 18/06/1999 | D.C. United | - | Los Angeles Galaxy | 1:2 |  |
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| 4. Round | 25/06/1999 | D.C. United | - | Kansas City Wizards | 3:0 | ||||
| 5. Round | 03/07/1999 | San Jose Clash | - | D.C. United | n.P. | ||||
| 5. Round | 06/07/1999 | Columbus Crew | - | D.C. United | n.P. | |
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| 7. Round | 03/09/1999 | D.C. United | - | Dallas Burn | 4:1 | ||||
| 7. Round | 09/09/1999 | Tampa Bay Mutiny | - | D.C. United | 1:2 | ||||
| 7. Round | 17/09/1999 | D.C. United | - | MetroStars | n.P. | ||||
| 8. Round | 05/10/1999 | D.C. United | - | Tampa Bay Mutiny | 2:4 | ||||
| 8. Round | 08/10/1999 | D.C. United | - | New England Revolution | n.P. |
Colombia